Monoazodyestuffs



Patented Mar. 30, 1937 I UNITED STATES PATENT OFFICE No Drawing. Application February 11, 1935, Serial No. 6,090.- In Germany February"24,

1934 i 4 Claims.

The present invention relates to new monoazodyestufis, more particularly it relates to azodyestufis which may be represented by the general formula:

wherein x stands for a non-acid substituent, such as alkyl; aralkyl; aryl; an etherified hydroxy group, for instance, alkoxy, aralkoxy and aryloxy; R stands for alkyl, aryl, aralkyl, alkoxy, aryloxy or aralkoxy, or the aminogroup, in which amino group the hydrogen atoms may partially or wholly be substituted by alkyl, aryl or aralkyl, and R stands for the radical of a 2-aminonaphthalenesulfonic acid including a Z-amino-naphthalene sulfonic acid, 2-amino-8-hydroxynaphthalene-6- sulfonic acid and N-alkyl and N-hydroxy-alkyl substitution products thereof which has been coupled in an acid medium.

Our new dyestufis are obtainable by diazotizing in the usual manner with sodium nitrite and hydrochloric acid an amine of the general formula:

wherein x and R mean the same as stated above, and coupling in an acid medium with a 2-aminonaphthalene-sulfonic acid or a substitution product thereof.

The new dyestufis generally dye wool even violet to blue shades of good fastness to fulling, and the dyeings obtained can be distinguished by a good evening color.

The invention is illustrated by the following examples, without being limited thereto:

Example 1.351 parts by weight of 5-nitro- 2-amino-1-methoxy benzene-3-sulfoethylanilide are diazotized with 69 parts by weight of sodium nitrite and hydrochloric acid. The diazo solution is introduced into an acetic acid solution of 239 parts by weight of 2-amino-8-hydroxynaphthalene-6-su1fonic acid, and the reaction acid to Congo is neutralized with sodium acetate. The isolated dyestuif having in the free state the i01- lowing formula:

OCH: HO

OIN N=N l I S O: N

dyes wool from an acid bath clear greenish-blue shades of excellent evening color.

Example 3.--324 parts by weight of 5-nitro-2- amino-1-methoxy-benzene-3-sulfonic acid-phen yl ester are diotized with 69 parts by weight of sodium nitrite and hydrochloric acid and coupled in an acetic acid medium with 239 parts by weight of 2-amino- 8 -hydroxynaphthalene 6 sulfonic acid. The isolated dyestufi having in the free consisting of alkyl, aryl, aralkyl, alkoxy, aryloxy,

state the following formula: aralkoxy, amino and alkyl-, aryland aralkyl- S 03H amino groups, and R stands for the radical of a 2-amino-napthalene sulfonic acid which has been coupled in an acid medium, dyeing wool generally even violet to blue shades of good fastness to fulling.

2. Azodyestufis of the general formula:

(5O: OIN N=NR' wherein :n stands for an etherified hydroxy group R stands for a substituent selected from the group dyes wool from an acid bath greenish-blue shades. consisting of alkyl, aryl, aralkyl, alkoxy, aryloxy,

In the following table there are given further aralkoxy, amino and alkylaryland aralkylcombinations prepared in accordance with the amino groups, and R stands for the radical of directions given in Example 3 and the shades a coupling component selected from the group obtained on wool: consisting of 2-aminonaphthalene-sulfonic acid, 2-amino-8-hydroxynaphthalene-6-sulfonic acid Coupled in an acid and N-alkyl and N-hydroxyalkyl substitution Dmotlzed medium with- Shade on W001 products thereof which has been coupled in an acid medium, dyeing wool generally even violet s-nitm-z-amino-i-meth- 2-amino-8- ye to blue shades of good fastness to fulling.

ybenzene'g'suuomc dmxynaphtha' 3. The azodyestuff of the following formula:

5 mm HO fi-nltro- 2-amino l'-methyl-' 2 amino 8 hy- Reddish-violet.

benzyl ester. long 6 sulfonic aci 5-nitro-2-amino-1-methyldo Reddish-violet. aH

blelnzelie d3 sulloethylp any am e. 30 Do 2-methylamino- Bluish-vlolet. 00H: HO

' 8 -hlt1ty(}roxy nap aenc-G- sulionlc acid. :N =N Do 2 mfitltilylaming- Violet.

nap aenesullonic acid. I 02 NH; I

benzene 3 sulloethylbendroxynaphthaliq-01H! zylamide. lene 6 sulfonic acid. 2 amino 3 methoxy 5 do Reddish-blue.

nitrophenylmethyl-sullone. 2 amino 3 methoxy 5 do Blue.

nitrophenylbenzyl-sulfone. 40 6 nitgo 2 flmillilfl -dmethdo Reddish-blue.

oxy enzene-3-su ami e. 5 nitro 2 amino l meth- 2 hydroxyethyl- Greenish-blue. dyglng W001 from an acld bath Clear blue shades yg ngg a 3 sulfoethyl- 3 32 gywhich do not change in artificial light and which p e y ymg u are fast to fulling.

acid. 4 5 mm 2 amino 1 mew 2 methylamims Do The azodyestufi of the following formula.

oxybenzene 3 sulfo hyhydroxynaph- S O H droxyethylphenylamide. thalene 6 sul- D tonic acid.8 h B1 0 Z-aminoyue.

droxynaphtha- HO lens 6 sulionic 8C1 v 5O 5 nitro 2 amino -1- methdo Do. O

oxybenzene-S-sulfonic acid- I methylester. s /N We cla N-C2Hi H \CHI 1. Azodyestuifs of the general formula:

OflN N=NR dyeing wool from an acid bath clear greenish- 802R blue shades of excellent evening color.

wherein .1: stands for an etherified hydroxy group, PAUL ZERVAS.

R stands for a substituent selected from the group HEINRICH CLINGESTEIN. 

